TRANS-4-HYDROXY-N-TRIPHENYLMETHYL-L-PROLINE METHYL ESTER

Base Information

• Chemical Name: TRANS-4-HYDROXY-N-TRIPHENYLMETHYL-L-PROLINE METHYL ESTER
• CAS No.: 129430-93-9
• Molecular Formula: C25H25 N O3
• Molecular Weight: 387.478
• Mol file: 129430-93-9.mol

Synonyms:L-Proline,4-hydroxy-1-(triphenylmethyl)-, methyl ester, cis-;cis-4-Hydroxy-N-(triphenylmethyl)-L-proline methyl ester

Chemical Property of TRANS-4-HYDROXY-N-TRIPHENYLMETHYL-L-PROLINE METHYL ESTER

Chemical Property:

• Vapor Pressure: 5.82E-11mmHg at 25°C
• Refractive Index: 1.618
• Boiling Point: 503.6°C at 760 mmHg
• Flash Point: 258.3°C
• PSA: 49.77000
• Density: 1.211g/cm³
• LogP: 3.52460
• Storage Temp.: 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

(2S,4S)-Methyl4-hydroxy-1-tritylpyrrolidine-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TRANS-4-HYDROXY-N-TRIPHENYLMETHYL-L-PROLINE METHYL ESTER

There total 12 articles about TRANS-4-HYDROXY-N-TRIPHENYLMETHYL-L-PROLINE METHYL ESTER which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

methanol (67-56-1) + 5-triphenylmethyl-2-oxa-5-aza-bicyclo<2.2.1>heptan-3-one (124456-35-5) → (2S,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate (129430-93-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 48h; Ambient temperature;

Reference yield: 76.0%

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) + trityl chloride (76-83-5) → methyl (2S,4R)-4-hydroxy-1-tritylpyrrolidine-2-carboxylate (129430-93-9,129430-94-0)

Guidance literature:

With triethylamine; In chloroform; at 0 ℃;

DOI:10.1016/S0040-4039(97)10793-6

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) + trityl chloride (76-83-5) → (2S,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate (129430-93-9)

Guidance literature:

L-4-hydroxyproline methyl ester hydrochloride; trityl chloride; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

With benzoic acid; 1,2-bis-(diphenylphosphino)ethane; diethylazodicarboxylate; In toluene; at 20 ℃; for 2h;

With potassium hydroxide; In methanol; for 2h;

DOI:10.1016/j.tetlet.2003.08.075

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride

trityl chloride

bromo-triphenyl-methane

(R)-4-hydroxy-L-proline ethyl ester

Downstream raw materials:

cis-4-hydroxy-L-proline methyl ester 4-toluenesulfonate

cis-L-hydroxyproline methyl ester

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

(2S,4R)-4-fluoropyrrolidine-2-carboxylic acid

Refernces

• 1、 Kehat, Tzofit,Portnoy, Moshe. "Polymer-supported proline-decorated dendrons: Dendritic effect in asymmetric aldol reaction". . p. 2823 - 2825. Retrieved 2008/02/10.
• 2、 Demange, Luc,Menez, Andre,Dugave, Christophe. "Practical synthesis of Boc and Fmoc protected 4-fluoro and 4-difluoroprolines from trans-4-hydroxyproline". . p. 1169 - 1172. Retrieved 2007/10/03.